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Kissimmee Vacation Rentals

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3168 rentals in Kissimmee.
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Superb 4 Bedroom Home, just 3 minutes from Disney, vacation rental in Kissimmee

Superb 4 Bedroom Home, just 3 minutes from Disney

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Disney 5 Star Vacations / The Osprey Villa, vacation rental in Kissimmee

Disney 5 Star Vacations / The Osprey Villa

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Seasons Villa,5 Bedrooms, Pool with Spa, Gameroom Sleeps 10, vacation rental in Kissimmee

Seasons Villa,5 Bedrooms, Pool with Spa, Gameroom Sleeps 10

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Debbie's Florida Retreat a Luxury Vacation Home, vacation rental in Kissimmee

Debbie's Florida Retreat a Luxury Vacation Home

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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A stunning pool home in Kissimmee, Disney Paradi, vacation rental in Kissimmee

A stunning pool home in Kissimmee, Disney Paradi

4 bedrooms
3 bathrooms
Sleeps 9
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Contact us for discount on 2021 openings, vacation rental in Kissimmee

Contact us for discount on 2021 openings

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Kissimmee Disney Villa with Wireless Internet, vacation rental in Kissimmee

Kissimmee Disney Villa with Wireless Internet

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Star Lake Villa, close to Disney with pool, vacation rental in Kissimmee

Star Lake Villa, close to Disney with pool

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sonshines Florida Villa, Peaceful Getaway  and Pool, vacation rental in Kissimmee

Sonshines Florida Villa, Peaceful Getaway and Pool

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Family-Friendly Large Villa with a Pool, Jacuzzi,, vacation rental in Kissimmee

Family-Friendly Large Villa with a Pool, Jacuzzi,

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Spacious 4-bed lakeside pool villa near Disney, vacation rental in Kissimmee

Spacious 4-bed lakeside pool villa near Disney

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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DisneyVacationRental 3BR 2Bath w Pool heat from $85/night, vacation rental in Kissimmee

DisneyVacationRental 3BR 2Bath w Pool heat from $85/night

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Belle's Cove, Family-Friendly Villa with Gameroom and Hot Tub, vacation rental in Kissimmee

Belle's Cove, Family-Friendly Villa with Gameroom and Hot Tub

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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2675CA - Sonoma Resort, vacation rental in Kissimmee

2675CA - Sonoma Resort

6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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The Charming Mickey's Tree House,, vacation rental in Kissimmee

The Charming Mickey's Tree House,

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Disney Family Villa pool/spa/games room, 5 bds 4 bathrooms, 15 Mins to Disney, vacation rental in Kissimmee

Disney Family Villa pool/spa/games room, 5 bds 4 bathrooms, 15 Mins to Disney

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Lovely Affordable Ground Floor Condo at Cane Island Resort, vacation rental in Kissimmee

Lovely Affordable Ground Floor Condo at Cane Island Resort

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hideaway Villa,Terra Verde Resort - Xbox,PS2,Games Room, Pool, vacation rental in Kissimmee

Hideaway Villa,Terra Verde Resort - Xbox,PS2,Games Room, Pool

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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The Emerald Dolphin, Kissimmee Rental with WiFi, Hot Tub and Pool, vacation rental in Kissimmee

The Emerald Dolphin, Kissimmee Rental with WiFi, Hot Tub and Pool

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Superior Home with Private Pool, 4307, vacation rental in Kissimmee

Superior Home with Private Pool, 4307

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Lake Berkley Holiday Villa with FREE pool heating., vacation rental in Kissimmee

Lake Berkley Holiday Villa with FREE pool heating.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Executive 4 Bedroom / 3 Bathroom Lake View Home in Gated Resort Community, vacation rental in Kissimmee

Executive 4 Bedroom / 3 Bathroom Lake View Home in Gated Resort Community

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Magical Pool Villa - 4 Miles to Disney!, vacation rental in Kissimmee

Magical Pool Villa - 4 Miles to Disney!

7 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Bass Lake Beauty with a Pool, WiFi and Air Conditioning, vacation rental in Kissimmee

Bass Lake Beauty with a Pool, WiFi and Air Conditioning

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower., vacation rental in Kissimmee

Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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2615CALISTOGA, vacation rental in Kissimmee

2615CALISTOGA

9 bedrooms
5 bathrooms
Sleeps 23
Match: Sleeps
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Tranquil Holiday Home-Games Room, Private Pool, WiFi, Disney/Orlando, vacation rental in Kissimmee

Tranquil Holiday Home-Games Room, Private Pool, WiFi, Disney/Orlando

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bella Vida Resort 5 Bedroom Vacation Home with Pool (1870), vacation rental in Kissimmee

Bella Vida Resort 5 Bedroom Vacation Home with Pool (1870)

5 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Disney Dream Villa At CLC Encantada Resort, vacation rental in Kissimmee

Disney Dream Villa At CLC Encantada Resort

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chris and Sue's Disney Condo at Windsor Palms Resort, vacation rental in Kissimmee

Chris and Sue's Disney Condo at Windsor Palms Resort

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Charming Townhouse with Pool and Tennis Court in Gated Community, vacation rental in Kissimmee

Charming Townhouse with Pool and Tennis Court in Gated Community

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Family Resort - 6BR Luxury Home - Private Pool, BBQ and Theater, vacation rental in Kissimmee

Family Resort - 6BR Luxury Home - Private Pool, BBQ and Theater

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney, vacation rental in Kissimmee

Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Disney World Area, Pet-Friendly, Vacation Home, vacation rental in Kissimmee

Disney World Area, Pet-Friendly, Vacation Home

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Villa Linton - Beautiful Florida Home with Themed Bedrooms, vacation rental in Kissimmee

Villa Linton - Beautiful Florida Home with Themed Bedrooms

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Villa Paradiso (2642 TV), vacation rental in Kissimmee

Villa Paradiso (2642 TV)

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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villanirvana, vacation rental in Kissimmee

villanirvana

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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5 bedroom 5 bathroom in Storey Lake 4740SHD, vacation rental in Kissimmee

5 bedroom 5 bathroom in Storey Lake 4740SHD

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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5 bedroom villa with private pool in gated resort., vacation rental in Kissimmee

5 bedroom villa with private pool in gated resort.

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Private Villa with Security Gate, Sunset Lakes in Kissimmee, vacation rental in Kissimmee

Private Villa with Security Gate, Sunset Lakes in Kissimmee

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Large Pet Friendly Home, 4445, vacation rental in Kissimmee

Beautiful Large Pet Friendly Home, 4445

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Stunning 5 Bd w/ Pool Close to Disney * Storey Lake 2767, vacation rental in Kissimmee

Stunning 5 Bd w/ Pool Close to Disney * Storey Lake 2767

5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Storey Lake upscale Unit, vacation rental in Kissimmee

Storey Lake upscale Unit

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious 5 Bedroom / 3 Bathroom Villa at Lake Berkley - Southern Exposure!, vacation rental in Kissimmee

Luxurious 5 Bedroom / 3 Bathroom Villa at Lake Berkley - Southern Exposure!

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Fantasy Pool Home, vacation rental in Kissimmee

Fantasy Pool Home

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Grandmas's Ami (4907TV) - Trafalgar Village, vacation rental in Kissimmee

Grandmas's Ami (4907TV) - Trafalgar Village

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Modern 3 Bedroom Condo, Sleeps 6+, 2 Miles to Disney, vacation rental in Kissimmee

Modern 3 Bedroom Condo, Sleeps 6+, 2 Miles to Disney

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Exquisite Villa with Private Pool/Spa & Games Room, vacation rental in Kissimmee

Exquisite Villa with Private Pool/Spa & Games Room

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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VP2522DC - 4 beds pool home - Gated resort, vacation rental in Kissimmee

VP2522DC - 4 beds pool home - Gated resort

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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*CLEAN - Afforable Townhome - 5 Miles from Disney*, vacation rental in Kissimmee

*CLEAN - Afforable Townhome - 5 Miles from Disney*

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Frequently Asked Questions about Kissimmee





About Kissimmee
Kissimmee, Florida is a budget-lover's dream with easy access to Disney parks for a fraction of the cost. Smart vacationers know that searching for a vacation rental in Kissimmee, Florida often gets you space, luxury and a great rate. This area also boasts plenty of natural beauty with a number of public parks. Kissimmee is an active community with bike trails and abundant golf courses. Baseball fans can enjoy a spring training game as Kissimmee is the (February) home of the Houston Astros.
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About Kissimmee
Kissimmee, Florida is a budget-lover's dream with easy access to Disney parks for a fraction of the cost. Smart vacationers know that searching for a vacation rental in Kissimmee, Florida often gets you space, luxury and a great rate. This area also boasts plenty of natural beauty with a number of public parks. Kissimmee is an active community with bike trails and abundant golf courses. Baseball fans can enjoy a spring training game as Kissimmee is the (February) home of the Houston Astros.
Kissimmee Vacation Rentals
Whether you’re interested in a one-bedroom condo rental in Kissimmee or a seven-bedroom luxury villa, booking a vacation rental on TripAdvisor makes your selection easy. Families that do the math will realize renting a condo or villa with multiple bedrooms in Kissimmee will be much, much cheaper than staying at a theme park or resort. The rentals often come with special amenities like a pool, hot tub, movie theater, arcade, or patio with grill for cookouts. Since the theme parks come with extreme costs, you can save a ton by cooking meals in your full kitchen at home, rather than wasting it all at a restaurant three meals a day. You’ll even save money on baggage fees with a rental—when you’ve got your own washer and dryer, you can do a few loads of laundry and pack much less clothing.
Things to do in Kissimmee
Don’t forget, there’s more to this part of Florida than Mickey and Donald and friends. From go-kart racing and miniature golf to water parks and adventure sports, Kissimmee offers family-oriented activities to suit any taste. Animal lovers will want to spend a day at Sea World, or take a day trip to the Everglades. Shoppers should save time (and suitcase space) for bargain-hunting at outlets in Kissimmee and the nearby Orlando Premium Outlets. Every Saturday night in Old Town Kissimmee, there is a classic car cruise through the city streets, accompanied by a live band. This downtown area also has plenty of shopping and restaurants for the entire family. Named after Florida's most famous reptile, Gatorland is a giant animal theme park with lots of wildlife. Bring the kids to Kissimmee Lakefront Park which is perfect for family picnics and exploring the lighthouse. Travel back in time at Oscaloosa County Pioneer Village and experience what life was like for early settlers.